2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal
• CAS No.: 78009-76-4
• Molecular Formula: C₃₆H₅₂O₄S₂Si
• Molecular Weight: 641.024
• Mol file: 78009-76-4.mol

Synonyms:2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal

Chemical Property of 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal

There total 1 articles about 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal (13036-07-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal (78009-76-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 72h; Ambient temperature;

DOI:10.1139/v81-044

Reference yield: 99.0%

2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal (78009-76-4) → 2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose (78009-77-5)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetone; for 1h; Ambient temperature;

DOI:10.1139/v81-044

Reference yield:

2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl-D-arabinose diethyl dithioacetal (78009-76-4) → (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-13-(2-hexyl-[1,3]dioxolan-2-yl)-tridec-6-en-2-ol (78009-95-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / HgCl₂, HgO / H₂O; acetone / 1 h / Ambient temperature

3: 1.) 0.59 N EtONa, ozone; 2.) sodium hydride / 1.) ethanol; 2.) ethanol

4: 77 percent / pyridinium chlorochromate, sodium acetate, Celite / CH₂Cl₂ / 2 h / Ambient temperature

5: 86 percent / 1.) 1.6 M n-BuLi / 1.) hexane, THF; 2.) THF, hexane

6: 90 percent / m-chloroperbenzoic acid / 4.5 h / Ambient temperature

7: 1.) 0.50 M lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 30 min; 2.) 30 min, THF

8: 84 percent / 0.65 N tetra-n-butyl-ammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

With n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium ethanolate; sodium acetate; sodium hydride; ozone; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diphenylphosphide; mercury dichloride; mercury(II) oxide; methyl iodide; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1139/v81-044

upstream raw materials:

2,3,5-Tri-O-benzyl-D-arabinose-diethylmercaptal

tert-butyldimethylsilyl chloride

Downstream raw materials:

2,3,5-tri-O-benzyl-4-O-(tert-butyldimethylsilyl)-aldehydo-D-arabinose

1,4-anhydro-2,3,5-tri-O-benzyl-D-arabinitol

(2R,3S,4R)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol

((1R,2S,3S)-2,3-Bis-benzyloxy-1-benzyloxymethyl-4-iodo-butoxy)-tert-butyl-dimethyl-silane